Pimpin'
by pink.chocolate.unicorn
Summary: Why was Castiel looking like a stereotypical pimp from a bad 70's movie? Dean was pretty sure he was staring, but he figured it was expected when you see an angel of the Lord decked out, head to toe, in bright purple crushed velvet. And leopard print trim. (Rated M for language. Pimp!Cas and cross-dressing also afoot.)


_(A/N: Rated **M** for mature __language. [How many times can you say 'fuck' and still keep a **T** rating?]  
_

_Heh. Well, the icon picture is what inspired this little... uh... thing. The picture is not mine, of course. I'm terrible with tumblr, so I haven't a clue if I successfully tracked down who to credit this to (but I _think_ this is the proper source/link here: winchester-kelly . tumblr image/ 73556701830 [remove spaces]) so please don't sue me, or, like, boycott my funeral. (I will, of course, correct it if the proper source is found and shared.) I only used it as inspiration to bestow respect... and mildly inappropriate fanfiction on it. (I'm still amazed this didn't go straight into an M rating for smut... I really don't know what happened with that. -shrug-.)  
_

_Warnings: Language. Cross-dressing. Pimp!Cas. Terrible plot. __MalexMale slash (implied/non-explicit... sorry?)_

_Enjoy! :))_

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Dean Winchester's hand paused just before he went to knock on the cheery yellow door. He stared at his own hand, mostly at the cuff of the trench coat, as if he'd never seen it before. The tan sleeve and cuff was really the only thing that he was able to focus on for a few beats, staring blankly at it in confusion as he tried to remember why he'd be wearing such a thing.

What the fuck?

He looked to his right and nearly gaped when he saw his brother in a similar getup. Why the hell were they both wearing trench coats and standing in front of, what appeared to be, a sorority house? He wiggled his shoulders a little, trying to shake off the 'creeper in the park' feeling, and then looked over his shoulder. His eyes widened to cartoon character proportions, most likely, and he _probably_ made a really stupid noise that sounded like a turkey being stepped on.

Seriously. What the actual _fuck_?

Why was Castiel looking like a stereotypical pimp from a bad 70's movie? He was pretty sure he was staring, but he figured it was expected when you see an angel of the Lord decked out, head to toe, in bright purple crushed velvet. And leopard print trim every-fucking-where. Shit, Cas even had a cane and a big ass, wide-brimmed hat that matched the entire getup. OK, yeah; it was seriously a bad-ass pimp suit but he had no clue why Cas was wearing it. He was tempted to pinch himself but he didn't want to look like a lunatic.

"Uh," Dean said instead, still staring at the Pimp 'o the Lord and trying to figure out if he'd been roofie'd. Or doped with acid. Or _some_thing that had the image in front of him making any sort of sense.

"Dean!" Sam hissed, smacking his brother on the shoulder to get his attention away from Cas. Of all the times for his brother to go all gooey eyed... "I swear to god, if you're backing out now, I'm going to fucking kill you." He adjusted himself, trying not too be obvious about it, but how else could he get the freakin' string out of his ass crack? He glared again when Dean just looked at him blankly; like he had no clue where he was. Or that this insanity hadn't been his damn idea. Ugh, the jerk.

Dean blinked, taken aback by the tone and the fact that Sammy seemed more irked he was stalling than anything else. Did he not see Cas, mere feet away and _in his line of sight_, looking like Huggy Bear's demented cousin?

"Uh," he said again. He looked over his shoulder again. Yup, Cas was still there; leaning against his gold Pimp Mobile and still wearing his über tacky, crushed velvet Pimp Suit (and it was still horribly purple and trimmed in fake leopard print). He was still wearing the wide brimmed hat, and now Dean noticed the hat even had a big, long, red feather in the leopard hatband for fuck's sake. He sort of wanted Cas to strut over so he could see if the angel was wearing old school platform shoes, too.

"Dean," Sam sighed, pinching the bridge of his nose as he closed his eyes and counted to 10. Twice. He opened his eyes when he realized Cas was walking over and he pulled Dean away from the door by his elbow. They met Cas in the middle of the sidewalk. "What? What's wrong _now_?"

Castiel squinted his eyes slightly, his head cocked a bit to the side, as he looked between the Winchester brothers. "Is there a problem, Dean?"

"Yeah, Cas. I guess you could say there's a teensy problem."

Dean had no idea what the hell he was wearing under the trench coat, but he knew it wasn't jeans and a flannel. And something was digging into his butt crack and squeezing the hell outta his junk. Other than that, it was... well, kinda soft but still... pinchy. He looked between Cas and Sam, confused as to why they were both looking at him as if he were the problem. Did he have a stroke at some point and black out? Maybe this was a dream...? Although, honestly, if it was a dream, he was pretty sure Cas would be the one wearing the skimpy lingerie and he'd be the one all decked out and rockin' the pimp look.

And they'd probably be in the back of the Impala.

And Sam wouldn't even be here.

So; what the fuck? He still couldn't wrap his head around all the insanity.

"What is the problem, Dean?" Castiel asked, leaning forward a little and looking Dean over critically. Nothing _seemed_ wrong...

"What are we doing? Why am I wearing this ridiculous outfit?" Dean asked, trying his damnedest to ignore the fact that he was pretty sure his brother was in a similar situation. He really did not want to picture Sam—Ugh, too late. He promised his brain a thorough bleaching later; he'd need it to get the image of Sammy in a lacy thong out of his memory.

Castiel and Sam shared a look. "It was your idea," Castiel said patiently.

"_My idea_? What?! No way... I wouldn't willingly wear... this?" Dean said, waving a hand over himself and trying not to yell or pout. And he absolutely refused to find Cas' squinty eyes adorable. Mostly because it was a good sign the angel was experiencing one of the less-than-pleasant human emotions. Probably a lack of patience in this case... Pissy angels were no fun.

Castiel huffed softly. He was temped to whack Dean with, what he understood to be, his Pimp Cane. Or maybe he was supposed to use his Pimp Hand? Either way... he wanted to smack Dean Winchester but he knew it wouldn't help. And they'd already argued about this earlier, for an hour, and he hadn't been able to change Dean's mind _then_. It was extremely irritating that Dean felt the need to remind him...

"You said I couldn't dance. You also refused to let me wear that outfit." Castiel nodded at Dean with his chin, indicating the outfit the Hunter wore underneath the tan trench coat. He didn't like the outer garment on the Hunter, it was just... odd for reasons he didn't quite understand. But he knew better than to say that aloud. Dean would get grumpy. And a grumpy Dean tried his patience and did weird things to his stomach.

Dean nodded a little. That definitely sounded like something he'd say. Though, Cas really _could_ dance; he'd learned rather quickly how to move his feet (and hips) once they watched a few 'educational tapes' and went out to see some live strippers and exotic dancers. Dean's chin nearly hit his chest when he saw Cas squirming around to a bass-heavy song as he practiced, giving Dean a proud little grin as he finished. He could really see how it woulda been... difficult to imagine people seeing Cas like that. _In lingerie_. Especially with the way the angel moved as he danced. It was just—_No_. Not gonna happen; not if he had any say in the matter.

Son of a bitch.

Yeah, he could get why he'd be such an ass about it and they were currently in the situation they were in. God, he could be such an idiot at times...

Dean looked back at Sam and cringed a little. His aversion to anyone seeing Cas writhe around in silk and lace had lead to this; he'd been left with the default option of having _Sam_ do this with him. Yeah, he was a complete idiot and he had to remember which fucking brain to think with more often. He really hoped it wouldn't lead to wearing lingerie, and pervy trench coats, with his brother too often. But one never knew with the kinda luck he had.

And just what the hell were they even doing that required... _this_ to be a plan?

"Yeah, yeah, of course. So. What's the plan?"

Sam glared at Dean and adjusted himself again. He was sincerely regretting the fact they didn't have the time to see if they made lingerie for men*. It would probably fit a little better. "We're here to snoop. And since some _genius_—" He paused and glared at Dean again, and Dean was glad his brother couldn't kill with looks alone. "—showed up as a cop earlier, without a plan or a word to anyone else, the girls freaked and wouldn't let him in without a warrant."

"No way," Dean said, eyes widening a little. He stoically ignored Sam's epic bitch face and tried not to pout. Since when couldn't he charm a girl (or a houseful of girls, apparently) into doing his bidding? As if Sam read his mind, the death glare was back and he shrugged sheepishly. He cleared his throat and tried not to fidget or squirm since it would only make things ride up and pinch some more. "So... this is plan B?"

Sam nodded, pulling his trench coat around himself a little tighter. "Yup. Cas overheard them talking about one of the girl's getting engaged, and it kinda went from there." He had sort of known there was such a thing as male strippers... but he was stunned to realize it was not at all out of the ordinary for them to wear women's lingerie. _By request_. Just when he thought he could sort of understand the female brain, _this_ happened. Stupid Dean with his stupid ideas...

"Okay," Dean said slowly, exhaling. "So—we're strippers." He didn't get why they needed the pimped out angel but he figured they needed Cas to come along and he needed to 'fit in' somehow. As if the walking purple eye-sore he currently was '_fit in_' anywhere.

Sam nodded, eyeing Dean warily. "Yeah, did you _conveniently_ forget all this since this morning?"

"Uh, no. I just was making sure we all knew the plan," Dean said, nodding and feeling damn proud of himself for his quick thinking. Apparently, Sam wasn't as convinced and he was given another massive Bitch Face, but at least he didn't start whining or yelling at him again. "So, we doin' this?" he asked, clapping his hands together and nodding towards the house.

Sam sighed, rolling his eyes upwards, but he nodded. This better work or he was going to kill his brother with his bare hands.

They made their way back to the front door, Cas following behind in an exaggerated limping gait (dude took his role seriously), and knocked on the door. It wasn't long at all before the door was practically thrown open and a chorus of feminine squeals and giggles erupted. It took all of his restraint not to wince or turn around and make a break for freedom—demonically possessed shit be-damned!

On second thought, he vowed to himself as he was groped and pulled inside by a swarm of madly giggling women, even if this did work he was going to kill Dean with his bare hands.

}8{

Castiel watched the Winchesters get dragged into the living room, at least three girls attached to each of their arms (trying his hardest to ignore the pair of women following and staring covetously at Dean's ass and making grabby hands towards it), and reluctantly slipped down the hallway. While he was grateful to have been ignored by the excited females, leaving him a chance to snoop as instructed, he was a bit concerned for Dean and Sam's safety. He tried to shake off his doubts and got busy snooping.

He didn't know exactly what he was looking for, but Sam had been confident he'd 'know it when he saw it'. Whatever that meant.

}8{

Sam tried his best not to glare, or run away, when a large boombox was pulled out of thin air. A rap song started blasting out as the group of girls started screaming and clapping, a chant of 'strip!' and 'get goin' boys!' almost drowning out the music. He had hoped Cas would use his angel mojo and find the stupid demonically possessed book the second they'd walked in. But apparently, he didn't—or they'd be back in the Impala by now and this nightmare would be over before it had to get started.

He looked at Dean and nearly gaped when he saw his brother completely at ease and doing a strip-tease, grinning and gyrating at a group of girls that were inches away from him. Oh god.

"C'mon, Satin!" Dean said, grinning at a frozen Sam. He chuckled, thoroughly amused with himself and his cleverness—Satin was an awesome stripper name.

He gave his attention back to the gathering of overly-caffeinated women and slowly undid the belt around his waist. It was a real ego boost to hear an immediate surge in the noise, girly screaming and clapping, as he teased the strip of material from the loops. Hopefully, Sam wasn't standing there like a brooding Sasquatch and got down to business, too. But he didn't look, just in case Sam had decided to get into it. He didn't really need to see that and he was pretty sure it wouldn't take much for the hoard of crazed women to smoosh them together and demand they 'interact'.

He shimmied out of his trench coat, one shoulder at a time, giving a look he hoped was teasing and coy as he slowly slid the tan material down. Screams and wolf-whistles nearly deafened him and he took a moment to look down, curious to see what he was wearing. He nearly covered himself before he remembered he was _supposed_ to be wearing tiny, black lacy boy-short looking things. And there was a matching top that was, thank god, not a bra or anything too girly. He wasn't too bothered by it being way too tight and way too see-through.

He flexed his pecs and grinned when the group of women screamed and whistled their appreciation again. This wasn't so bad... Another wiggle and flex caused another fresh round of screams. Stripping was easy peasy. He turned to see what Sam was doing when the decibel level rose dramatically and he didn't know if he should laugh or rescue his brother when he looked over to see Sam trying to politely unclasp a girl's hand from his ass and another one from trying to get her whole hand down the front of his bikini thong thing. The women were smart, working together to keep Sam's attention divided as he tried to wriggle away. It really only served to make it look like Sam was dancing dirty and rubbing his junk against the gathered women as he tried to dodge away.

If that tug of war kept up, Sam's tiny red thong was going to come off. Of course, the women figured that out soon enough and Sam was mobbed and red stretchy fabric went flying. He hoped it was only the thin strapped top Sam had been wearing and not his tiny thong panties.

Oops. Even if they weren't real strippers, he needed to save his brother. And he was pretty sure people weren't meant to grab a handful of skin; keep your hands to yourself applied to male strippers, too... right? Plus, Sam would probably start screaming like a girl about his virtue. (Not that Dean could blame him; the sounds were going into inhuman levels and he was starting to worry he'd find pieces of his brother.)

Dean wiggled his way over, thankfully forgotten for a moment when the other girls scented naked man-flesh and paid him no mind, and he quickly pulled Sam out of the pile of girls. He didn't realize how strong a group of determined women were, because holy shit, he had to really pull and yank on poor Sammy's arm to get him free. As soon as he had his brother free from pawing hands, he tossed Sam his trench coat. Thankfully, that hadn't been torn to ribbons.

"Ah ah!" Dean said, shaking his finger as the group's focus quickly shifted to him. Where the hell was Cas? This was getting to be a little too much... He ignored the chorus of sad little 'aw!'s and shrugged back into his own trench coat the moment he saw a flash of purple from the corner of his eye. Cas, the dick, didn't pause to collect (or help) them; he just walked—well, _strutted_—right out of the front door, his purple Pimp coat flapping dramatically as he swept the door open with a flourish.

Dean grabbed Sam and pushed him towards the front door, too. He turned towards the advancing group of girls, offering his most charming smile. He affixed an apologetic expression on his face and raised his hands up. Hopefully they wouldn't pounce... "Time's up, ladies!"

Sam didn't wait around, he took off the moment he realized Cas had slipped back outside and Dean had the mob distracted. He really _really_ hoped that meant the angel found something and hadn't just given up and went to sulk in the car. He felt a little bad he didn't wait for Dean, but Dean hadn't been pawed and stripped roughly by a group of crazy college girls. He shuddered lightly, tucking his trench around himself tighter. He'd probably feel those sharp nails in delicate places and hear those high-pitched giggles for awhile...

He jumped a little when Dean was suddenly at his side and clapping him on the shoulder. He sent his brother a glare, annoyed to see the big ass grin on Dean's face. Jerk; _he_ wasn't mauled and roughly stripped naked by a pack of wild women. Of course, he knew saying anything about it would only have his assface brother teasing him, shaking his head sadly as if it should of been exciting or something.

"That wasn't so bad, eh, Sammy?"

"Shut up, Dean," Sam said without looking at his brother. He hurried over towards Cas, snickering again at the outfit the poor guy had to wear. It was ridiculously funny but Cas didn't see the humor in it so he refrained from out-right laughter. He shuffled closer and eyed the angel curiously. "Did you find it?"

Castiel nodded and pulled a small diary from the inside pocket of his Pimp coat. He didn't like holding it and he immediately handed it off to Sam, grateful the younger Winchester took it without question or hesitation. He noticed Sam's nose wrinkled in disgust for a moment before he tucked the diary into the pocket of his trench coat. "It took longer than I expected to find it. I do apologize."

"S'okay, Cas," Sam muttered, unsure why Cas was apologizing. Did the angel know his clothes had been torn off? He slowly turned and glared when Dean had the nerve to clap him on the shoulder and give him a shit-eating grin.

Dean just grinned wider at Sam's annoyed, bitchy face. Yeah, he'd probably be a little pissed in Sammy's shoes, but he actually had fun for a moment there. Plus, he was almost positive Cas had totally checked out his lacy ass when he walked by. Oh—And they got their demonic thingy. So, all around, a success and a good idea in his opinion. He totally _was_ a genius.

"Well, let's blow this popsicle stand, boys."

"—Dean!"

Dean jerked awake, nearly smacking his head into Cas' since the dumb angel with personal space issues was inches away from Dean's face when he bolted upright with a snort.

"What?" Dean asked, his voice fuzzy with sleep, as he wiped at the drool on his face. He really hoped he didn't get any drool on Baby's interior...

"We're nearly there," Cas said, settling back against the back seat once he was sure Dean was fully awake. Mostly he just needed a bit of distance because Dean had that annoyed look and he was very sure Dean would not appreciate it if he gave into his urge to fix Dean's hair. It was a mess on one side and all smooshed down on the other. It was ridiculous. And adorable. He folded his hands together and stared out of the window.

Dean rubbed at his eyes and nodded, yawning. Right; they were supposed to see Bobby about a demented diary some witch but a jinx on like a hundred years ago. So, all that... pimp and hoes shit _had_ been a dream. A really warped, fucked up dream. He probably should avoid mixing pizza and beer after 1 am if that was the kinda shit his brain was gonna come up with. He so didn't need the image of his brother in tight red spandex, or Cas in purple crushed velvet, ever again.

"What time is it?" he asked through another yawn, looking out the windows. There weren't many stars out anymore and he was pretty sure he could see a thin band of dark purple along the horizon...

Sam checked his watch, "Just after 5 am," he said. His eyes flicked over towards Dean for a moment. His brother was sitting there quietly, his head bobbing and nodding every so often as his eyes slowly drifted closed again. He felt bad for waking Dean after only a few hours, but he knew once they got to Bobby's they'd be running around like idiots as usual. "Roll the window down, Dean."

"Shuddup, Satin, or I'll give you a taste of my Pimp Hand," Dean muttered, trailing off with a low chuckle. He just shrugged when Sam (and Cas) gave him confused (and slightly offended) looks. He was so not going to get into that crazy-ass dream he had. Let them both think he was still half-asleep and talking nonsense. He rolled the window down, sucking in a breath when the cool air smacked him in the face. But it did an admirable job in chasing away the last remnants of sleep.

He sat back and just let the cool air continue its job in waking him up. Of course, now he was awake he didn't need to be thinking about getting Cas a sweet pimp cane... Or ways to sneak away his trench coat and dying it Pimpy Purple...

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_(A/N: *OMFG. They totally do make lingerie for men! Oh, it's so lovely, too! xdress. com and hommemystere . com ([remove spaces] both popped up when I did a quick search. I looked through both sites very thoroughly. Uhm... for research purposes... Yeah. Research.) Just thought I'd add that in there... _

_Oh... and I feel the need to clarify that I have seen (and reluctantly been a part of) a group of excited women around male strippers______—_and I feel like I've kept it rather toned down. Heh.  


_Carry on! :))_


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